Yes, two people that have the same address can both file Head of Household if there is more than one household and each taxpayer paid more than 50% of their respective households, it is possible to have more than one taxpayer meet the HOH filing status even if they live at the same place. For example, if you have adults that are living as roommates/housemates but each roommate has their own separate family (themselves and their dependents) and expenses that they are responsible for.